(Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether

Base Information

• Chemical Name: (Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether
• CAS No.: 729613-09-6
• Molecular Formula: C₂₀H₂₄BrFOSi
• Molecular Weight: 407.398
• Mol file: 729613-09-6.mol

Synonyms:(Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether

Chemical Property of (Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether

There total 2 articles about (Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether + ethyl vinyl ether (109-92-2,25104-37-4) → (Z)-3-fluoro-6-(tert-butyldiphenylsilyloxy)hex-3-en-2-one (129600-52-8) + (Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether (729613-09-6)

Guidance literature:

ethyl vinyl ether; With n-butyllithium; potassium tert-butylate; zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.666667h;

4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether; With triphenylphosphine; palladium diacetate; In tetrahydrofuran; hexane; at 10 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; hexane; water; at 20 ℃; for 0.25h;

DOI:10.1021/jo0604787

Reference yield:

tribromofluoromethane (353-54-8) + 3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) → (Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether (729613-09-6) + (E)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether (729613-18-7)

Guidance literature:

With diethylzinc; triphenylphosphine; In tetrahydrofuran; toluene; at 20 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1021/ol049742d

Reference yield: 77.0%

ethyl vinyl ether (109-92-2,25104-37-4) + (Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether (729613-09-6) → (E)-3-fluoro-6-(tert-butyldiphenylsilyloxy)hex-3-en-2-one (897393-32-7)

Guidance literature:

ethyl vinyl ether; With n-butyllithium; potassium tert-butylate; zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.666667h;

(Z)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether; With triphenylphosphine; palladium diacetate; In tetrahydrofuran; hexane; at 70 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; hexane; water; at 20 ℃; for 0.25h;

DOI:10.1021/jo0604787

upstream raw materials:

tribromofluoromethane

3-(tert-butyldiphenylsilyloxy)-1-propanal

ethyl vinyl ether

Downstream raw materials:

(E)-3-fluoro-6-(tert-butyldiphenylsilyloxy)hex-3-en-2-one